LU87884A1 - HERBICIDE-EFFECTIVE UREA DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF - Google Patents

Description

Herbicidal urea derivatives and methods for

Making the same

The invention relates to novel, herbicidally active, -substituted sulfonylurea derivatives of the general formula (I)

· - in what

Rf represents hydrogen, halogen, C 1-4 alkoxy, halo-Ci, _4-alkoxy, Ci_3-alkylsulfonyl or a group of the formula COR6; R2 represents hydrogen, C 1-4 alkyl or phenyl; R3 represents Ci.e-alkyl, C3_6 ~ alkenyl, a Cx ^ -alkoxyalkyl group, C2_4-alkyl or a benzyl group substituted by one or more halogens, R4 and R5 each independently represent a Cj ^ -alkyl, a C1 .4 is alkoxy, halogen, C ^ alkylamino or di (Cx_3-alkyl) amino or C ^ alkylthio;

Re for a C ^ alkoxy, C3_6 alkenyloxy, C3_6 alkoxyalkyl, Q.

3-alkylamino, di (Ci_3-alkyl) amino, piperazinyl or morpholinyl group; X represents oxygen or sulfur; and E represents a methine group or nitrogen, and their salts formed with alkali metals, alkaline earth metals, amines, or quaternary ammonium bases. The invention is further directed to herbicidal compositions which may contain such compounds together with an antidote.

The invention further relates to a process for the preparation of new compounds of the general formula (I), in which Rlr RZf R3, R4, R5, Rf, X and E are as defined above.

In the above definitions (throughout the description); ;; "alkyl group" means including a straight or branched alkyl group yj as. Methyl, ethyl, propyl, isopropyl as well as any of the isomers. Butyl groups; - "Alkoxy group" usually means. Methoxy, ethoxy, propoxy, isopropoxy or any of the four isomeric butoxy groups, especially a methoxy, ethoxy or propoxy group; - "Alkenyl group" can e.g. Allyl, isopropenyl, 1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-isobutenyl or a pentenyl group, in particular an allyl or 4-pentenyl group? "Halogen" as such or halogen of a haloalkoxy group can be fluorine, chlorine or 'bromine, in particular. Chlorine.

Suitable alkali metal or alkaline earth metal hydroxides, which form salts with the compounds of the general formula (Γ), are potassium, sodium, magnesium or calcium hydroxide, mainly sodium and potassium hydroxide.

Amines useful for salt formation include primary, secondary or tertiary amines such as methylamine, ethylamine, propylamine, isopropylamine, all four isomeric butylamines, dimethylamine, diethylamine, isopropylamine, diisopropylamine, pyrrolidine, piperidine, morpholine, trimethylamine, pyridine, quinoline or isoquinoline, especially isopropylamine and diethanolamine.

Quaternary ammonium bases used for salt formation are e.g. Tetraethylammonium, triethylbenzylammonium, trimethylbenzylammonium halide or any type of tetrabutylammonium halide.

Herbicidally active sulfonylurea derivatives are generally known compounds.

The known sulfonylureas are characterized in that the nitrogen substituted by a heterocyclic group in the 3-position is hydrogen or a C 1-4 alkyl group, preferably a methyl group; or a Ci_4-alkoxy group, preferably methoxy group; or "bears a C2_8 alkenyl, C2_ 4 alkynyl group or an aralkyl group. Other substituents have been published in a surprisingly small number of patent specifications.

Sulfonylureas of this type are e.g. in European Patent Specification No. 152,378 and Japanese Published Patent Application No. J5 8126872 and J6 0078981.

Sulfonylureas exert an excellent herbicidal action against a number of mono- and dicotyledon weeds, mainly broad-leaved and grass weeds [J.M. Green "et al .: Proc. S. Weed Sei. Soc. 34, 214 (1987)], particularly in wheat and barley crops. Their advantage is the very low effective doses (usually 5 to 50 g / hectare). Their disadvantage appears to be that crop plants are damaged to a greater or lesser extent after their use. When used in practice, it has been found that their antidoping with grains is advisable and essential with maize crops. In European patent application No. 127 469 Antidots are published which can be used after sowing in the pre-emergence period and which are able to protect wheat and millet from the harmful effects of herbicides of the sulfonylurea type.Methyl-2- [(aminocarbonyl) aminosulfonylj-benzoate and its ammonium salt as methyl 3- [(aminocarbonyl) aminosulfonyl] -2-thiophenecarboxylate was also found to be the cheapest.

According to the description of the United States patent no.

4,343,649, 1,8-naphthalic anhydride, α- (cyanomethoxyimino) benzene acetonitrile or N, N-diallyl-dichloroacetamide can be used to increase the selectivity of the herbicidally active 2-chloro-N- [(4-methoxy ~ 6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfonamide, 2,5-dichloro-N- [(4,6-dimethoxypyridin-2-yl) aminocarbonyl] benzenesulfonamide or 2-carbomethoxy-N - [(4,6-Dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide to achieve an advantageous result.

Herbicidal compositions containing a sulfonylurea derivative as an active ingredient together with glycine derivatives as an antidote are published in Hungarian Patent Specification No. 201 445.

The aim of the present invention was to develop herbicidal compositions which contain new active ingredients which have more advantageous physical and chemical properties, a higher selectivity and a lower persistence compared to. the known sulfonylureas' ~.

In the course of our investigations, compositions have been developed which contain new sulfonylurea derivatives of the general formula (I), which are characterized in that the N3 atom (nitrogen in the 3-position) of the sulfonylurea group substituted by a heterocyclic group forms a group R2-CH-OR3, wherein R2 and R3 are as defined above.

Compositions containing the new compounds of general formula (I) have been found to be particularly useful for weed control purposes since they exhibit excellent herbicidal activity at a suitable low dose, are selective to crops or by means of known antidotes can be made selective and at the same time can be easily broken down in the soil.

According to another aspect of the invention, a process for the preparation of the new compounds of the general formula (I) in inert organic solvents or mixtures thereof is provided. This procedure includes. . .. ..

a) the reaction of an isocyanate or isothiocyanate of the general formula (IV) .......

(IV)

wherein Rj is as defined above, with an aminopyrimidine or aminotriazine derivative of the general formula (III) • (III) wherein R2, R3) R4, R5 and E are as defined for formula (I), optionally in the presence of a base as Catalyst, at a temperature of 0 to 50 ° C, preferably between 20 ° C and 30 ° C; or

b) reacting a sulfonylcarbamate derivative of the general formula (V), (V) in which RI is as defined above and R is a phenyl group, with an aminopyrimidine or aminotriazine derivative of the general formula (III), in which R2 , R3, R4, R5 and E are as defined above, at a temperature of 25 to 120 ° C, preferably between 60 ° C and S0 ° C; or c) the reaction of a carbamoyl chloride of the general formula (VI)

(VI) | i wherein R2, R3, R4, R5 and E are as previously defined and R represents a phenyl group, with an alkali metal salt, one. Sulfonamides of the general formula (II)

(II) wherein Rx as defined for formula (I) in the presence of a base as catalyst at a temperature between -10 ° C and 50 ° C, preferably between 0 ° C and 50 ° C; or d) the reaction of an N-pyrimidinyl or N-triazinyl carbamate of the general formula (VII)

(VII) wherein R2, R3, R4, R5 and E are as defined above and R represents a phenyl group, with a sulfonamide of the general formula (II), wherein Rx is as defined for formula (I), in the presence of a catalytic amount of a base at a temperature of 20 to 80 ° C, preferably · between. 20 ° C and 40 ° C; or e) reacting a sulfonyl chloride of the general formula (VIII)

CVIII) in which Rx is as defined for formula (I), with an aminopyrimidine or aminotriazine derivative of the general formula (III) in which R2, R3, R4 and R5 are as defined above, and alkali metal cyanates at a temperature of 20 ° C to 120 ° C, preferably between 60 ° C and 90 ° C.

If desired, the compounds of general formula (I) which have been prepared using the above process variants can be converted into their salts with alkali metal or alkaline earth metal hydroxides, amines or quaternary ammonium halides, e.g. by reacting the desired compound with the appropriate base in a suitable solvent, which is subsequently evaporated.

In the preparation of compounds of general formula (I), both methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, tetrahydrofuran, acetonitrile, dioxane, benzene, toluene, xylene, chlorobenzene, dimethylformamide, nitromethane, nitroethane, N-methyletherpyrrolidone, dimethylethyryrolidone, dimethyl ,

Diisopropyl ether, dibutyl ether, hexane, petroleum ether,

Ethyl acetate, butyl acetate, dibutyl phthalate as well as mineral and vegetable oils can be used as inert organic solvents, but useful solvents are not limited to the above.

In the case of the above process variants, the reaction temperature can usually be varied within a wide range from -20 ° C. to the boiling point of the solvent used; however, it is preferred to use the components in one

Temperature between 0 ° C. and. 90 ° C, especially at 15 to 45 ° C, because. this temperature range is useful for also preparing the heat-sensitive derivatives of the general formula (I). The reactions are suitably carried out under atmospheric pressure, however an increased or: reduced pressure can also be used; the reactions can also be carried out in the presence of air or under an inert gas, e.g. Nitrogen- run: be.

To reduce the reaction time or to complete the reaction, a few drops of a base should be used as a catalyst.

In particular, both tertiary amines such as triethylamine, tributylamine, N, N-dimethylaniline and nitrogen-containing heterocyclic compounds, e.g. Pyridine or 1,4-diazabicyclo [2.2.2] octane (DABCO) can be used, although alkali metal hydroxides or alkali metal alkoxides such as sodium hydroxide or natriuramethoxide are also useful. The catalysts useful for carrying out the process variants are not restricted to those mentioned above.

The products divided by the above process variants can be separated by completely or partially evaporating off the solvent and recrystallization; or by rubbing an evaporation residue with a solvent or solvent mixture, which weakly dissolve the product. If necessary, the compounds obtained can be purified by chromatography on a suitable filling, such as aluminum oxide, silica gel and the like.

The compositions according to the invention usually contain the active ingredient of the general formula (I) in an amount of 0.01 to 95% by weight, preferably 2 to 80% by weight in the form of known formulations, e.g. Solutions, emulsions, dustable powders, suspensions, wettable powders, pastes, soluble powders, granules, suspension concentrates or emulsifiable concentrates, natural or synthetic impregnated with the active ingredient; Materials, or compositions encapsulated in polymeric substances.

The compositions are prepared by mixing and / or triturating the active ingredients with binders, solvents and / or carriers, if appropriate by simultaneously using both surface-active agents and / or dispersants and adhesion-promoting agents.

Useful solvents are: aromatic hydrocarbons, preferably C7.12 fractions, e.g. Toluene, xylene mixtures or substituted naphthalenes; chlorinated aliphatic or aromatic hydrocarbons, preferably chloroethylene, methylene chloride or chlorobenzene; aliphatic hydrocarbons such as cyclohexane, paraffins or mineral oil fractions; Mineral or vegetable oils; Alcohols, e.g. Ethanol or ethylene glycol; or their ethers such as ethylene glycol monomethyl ether, ethyl ether; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; strongly polar solvents, e.g. N-methylpyrrolidone,

Dimethylformamide, dimethylacetamide, dimethyl sulfoxide; Phthalic acid esters, e.g. Dibutyl phthalate or · dioleyl phthalate; as well as epoxidized vegetable oils such as epoxidized coconut oil or soybean oil; or water.

Suitable carriers are: inorganic powders such as kaolin, calcite, talc, chalk, quartz, attapulgite, montmorillonite, silica, pearlite, amorphous silicon dioxide, aluminum oxide, finely divided silica, pumice, brick powder, sepiolite, bentonite or sand; organic powders, e.g. flour-like powders made from parts of plants, such as corn stalks or coconut shells, and also corn flour; different types of starch, processed starch; Sugar, e.g. Glucose; powdered or ground synthetic resins, e.g. Phenolic or urea resins. In addition, a large number of inorganic or organic pre-granulated

Materials are used.

Nonionic, cationic and / or anionic surfactants can be used as surface-active agents which have advantageous emulsifying, dispersing and moisturizing properties. Mixtures of surfactants can also be used. The anionic surfactants are water soluble soaps, e.g. the sodium or potassium salt of oleic or stearic acid as well as the salts of natural fatty acid mixtures; however, it is more suitable to use synthetic surfactants, especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonate-benziraidazole derivatives or alkylarylsulfonates. The calcium or triethanolamine salts of lignosulfonic acids, dodecylsulfuric acid esters, from natural

Fatty acid-derived sulfonic acids as well as sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts, dodecylbenzenesulfonic acid or tributylnaphthalenesulfonic acid can be given as examples. In addition, phosphates, e.g. Salts of the phosphate ester of p-nonylphenol- (4-14) ethylene oxide adduct- are also suitable.

Quaternary amraonium salts can be considered as cationic surfactants which contain lower alkyl groups substituted by halogen or a hydroxy group and / or · in addition to a C 8-2o-alkyl group, a benzyl group bonded to the quaternary nitrogen. Examples of surfactants of this type are e.g. Stearyl trimethyl ammonium chloride or benzyl bis (2-chloroethyl) ethyl ammonium bromide.

The nonionic surfactants are mainly polyoxyethylene glycol ethers, polyoxyethylene glycol esters as well as esters of polyhydric alcohols and their condensation products, nonylphenol polyethoxyethanols, castor oil polyglycol ethers and polypropylene-polyethylene oxide adducts.

Lignin sulfonate, sulfite liquor and methyl cellulose are e.g. useful dispersants.

The compositions can include adhesion-promoting agents, e.g. Carboxymethyl cellulose, natural and artificial, powder-like, granulated or latex-like polymers, e.g. Polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalin, lecithin or. synthetic phospholipids. .......

In addition, the compositions according to the invention may contain other additives such as stabilizers, anti-foaming agents, viscosity regulators, preservatives and also inorganic or organic pigments.

Activating, synergistic and antidote substances can also be incorporated into the compositions according to the invention.

The herbicidal compositions which contain known antidotes such as DKA-24 (N-dichloroacetyl-N-allylglycine-N'-allylamide), AD-67 (N-dichloroacetyl-l-oxa-4-azaspiro [4,5] decane), R -25788 (N, N-diallyl-dichloroacetaraid), MG-191, TI-35 or CGA-92194 are also within the scope of the invention. (TI-35 is N- (dichloroacetyl) hexamethyleneimine, CGA-92194 is N- (1,3-dioxolan-2-yImethoxy) -imino-benzene-acetonitrile).

If desired, the compounds of general formula (I) according to the invention and the compositions containing them can be used in combination with other agricultural chemicals, which can be herbicides, fungicides, insecticides, miticides, nematocides, antiviral agents, plant growth regulators or attractants.

The compositions according to the invention preferably contain 0.01 to 95% by weight, more preferably 2 to 80% by weight of active ingredient of the general formula (I) or a total amount of active ingredient and antidote, 5 to 99.9% by weight of liquid or solid carrier and 0 to 30, preferably 0.1 to 25% by weight of surfactant or other additives.

In the compositions also containing an antidote, the ratio of antidote to active ingredient can be 1: 1 to 50: 1.

Compositions with the components listed below are particularly preferred (percentages are based on weight throughout): 1. Solutions

Active ingredient 1 to 30%, preferably 5 to 25% solvent 1. to 90%, preferably 0 to 85%

Surface active agent 0 to 99%, preferably 0 to 95% 2. Emulsifiable concentrate

Active ingredient 1 to 20%, preferably 5 to 10%

Surface active agent 1 to 30%, preferably 5 to 20%

Liquid carrier 50 to 94%, preferably 70 to 85% 3. Spray powder

Active ingredient 0.5 to 90%, preferably 20 to 80%

Surfactant 0.5 to 20%, preferably 5 to 15%

Liquid carrier 5 to 95%, preferably 15 to 90% 4th suspension concentrate '~ ·

Active ingredient 5 to 75%, preferably 10 to 50%

Water 25 to 95%, preferably 30 to 80%

Surfactant 1 to 40%, preferred. 5 'to 20% 5. powder

Active ingredient 0.5 to 10%, preferably 0.5 to 5% solid carrier 90 to 99.5%, preferably 95 to 99% 6. Granules

Active ingredient 0.5 to 30%, preferably 1 to 15%

Solid support 70 to 99.5%, preferably 85 to 95%

The compositions according to the invention can be diluted with water to a concentration of 0.01% by weight before use. The compositions can be applied to the area to be treated after or without dilution using the customary methods such as spraying, dusting, atomizing, spraying, sprinkling or using the ultra-low volume method. The inventive, containing the new sulfonylureas of the general formula (I)

Compositions have excellent herbicidal activity against both monocotyledonous and dicotyledonous, annual and perennial weeds. The-. · ..... - compositions according to the invention can be both. sowing as well as in the pre-emergence or · post-emergence period.

If the treatment is carried out without plants before the weeds emerge on the soil, they will sprout, plants will grow up to the cotyledon (cotyledon) phase, then their growth will stop and they will partially or die after 3 to 6 weeks completely off. If the treatment is carried out after weeding of the weeds, the growth of the weeds stops after the treatment and the weeds partially or completely die after 1 to 4 weeks. It is characteristic of the compositions according to the invention that they have an effect even in extremely small amounts. Depending on the weeds treated, the herbicidal activity is very good at doses as low as 0.01 to 2.0 kg / hectare. The important large-scale crops, e.g. Wheat, corn,

Barley, rice and soybeans were found to be resistant; thus, the compositions according to the invention are outstandingly suitable for controlling both monocotyledon and dicotyledonous, annual and perennial weeds which are difficult to kill or cannot be killed at all in the above crops. The crop plants are not limited to those mentioned above. Depending on the constituent used, doses of the compositions according to the invention from 0.05 to 2.0 kg / hectare can also be used to completely control the weeds.

A particular advantage of compositions which contain sulfonylureas of the general formula (I) as active constituents seems to be that they quickly decompose after they get into the soil; thus, if the compositions are used post-emergent, other crops may be sown on the treated area immediately after the host plant is harvested or after a shorter period of time compared to the known compositions containing commercially available sulfonylureas.

The production and use of the effective. Components / compounds of the general formula (() and compositions according to the invention are illustrated in detail in the following, non-limiting examples.

example 1

Preparation of 3-ethoxymethyl-1- (2-methoxycarbonylphenylsulfonyl) -3- (4-methoxy-6-methyl -1,3,5-triazin-2-yl) urea (Compound No. 8)

After adding 0.01 g of DABCO catalyst to a solution which contains 3.96 g (20 mmol) of 2-ethoxymethylamino-4-methoxy-6-methyl-1.3.5-triazine in 50 ml of anhydrous diethyl ether, 5. 3 g (22 × nmoles) of 2-methoxycarbonylphenylsulfonyl isocyanate dissolved in 20 ml of anhydrous diethyl ether were added dropwise to the above solution at room temperature with stirring. The reaction mixture is stirred for 6 hours, during which time product filling begins. The next day the crystalline precipitate is filtered, washed with a little diethyl ether and then dried at room temperature to give 6.5 g (74% yield) of the title product, mp: 105-106 ° C.

Example 2

Preparation of 3-ethoxymethyl-l- (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-l, 3,5-triazin-2-yl) urea (compound no.

4) 3.96 g (20 mmol) of 2- (ethoxymethyl) amino-4-methoxy-6-methyl-1.3.5-triazine are added to the solution of 6.23 g (20 mmol) of phenyl-N- (2-chlorophenylsulfonyl) ) carbamate in 120 ml of anhydrous benzene. The mixture is stirred at 75 to 80 ° C for 8 hours, then evaporated to dryness. After crystallization of the residue from diethyl ether, 5.06 g (61%) of the title compound are obtained, mp. 123-123 ° C.

Example 3 ...

Preparation of 3- (4,6-Dimethylpyrimidin-2-yl) -l- (2-chlorophenylsulfonyl) -3- (ethoxymethyl) urea £ (Compound No. 2) "4.87" g '(20 mmol) in 10 ml · dimethylformamide, dissolved 'N- (4,6-dimethylpyrimidin-2-yl) -N- (ethoxymethyl ·) -carbamoylchloride .. ". a 4.27 g (20 mmol) 2-chlorobenzenesulfonamide sodium salt in 25 ml of anhydrous solution containing redistilled dimethylformamide are added dropwise with stirring at 5 to 10 ° C. After the addition, the mixture is stirred for 3 hours at room temperature, then poured onto 250 ml of ice water, the precipitate is filtered, washed with a little water and dried and then recrystallized from a mixture of ethyl acetate and diethyl ether to give the title product in a yield of 3.34 g (42%), mp 118-119 ° C.

Example 4

Preparation of 3- (4,6-dimethylpyrimidin-2-yl) -3- (ethoxymethyl ·) —1— (2-methoxycarbonylphenylsulfonyl) urea (Compound No. 6)

After adding 3.1 g (10 mmol) of phenyl-N- (4,6-dimethylpyrimidin-2-yl) -N- (ethoxymethyl) carbamate to the solution of 2.15 g (10 mmol) of 2-methoxycarbonylbenzenesulfonamide and 1 , 52 g (10 mmol) l, 8-diazabicyclo [5.4.0] undec-7-ene in 25 ml anhydrous dioxane, the reaction mixture is stirred for 10 hours at 30 to 35 ° C, then poured into 200 ml · water. After adjusting the pH to 6.5, the precipitate is filtered, dried and then recrystallized from a mixture of chloroform and hexane to give 1.59 g (37.6%) of the title compound; Mp 124 to 126 ° C.

Example 5

Preparation of 3- (4,6-dimethylpyrimidin-2-yl) -3-methoxymethyl-l- (2-methoxycarbonylphenylsulfonyl) urea (compound no.

5) ......

A 4.3 g (20 mmol) 2-methoxycarbonylbenzenesulfonyl chloride, 3.67 g (22 mmol) 4,6-dimethyl-2- (methoxymethyl) aminopyrimidine and 3.24 g (40 mmol) potassium cyanate in 30 mL anhydrous acetonitrile heated to 81 ° C. for 2 hours with vigorous stirring. After filtering off the precipitated, inorganic salt, the filtrate is evaporated, the residue is resuspended in 30 ml of water, then the filtered off precipitate dried and recrystallized from a mixture of ethyl acetate and diethyl ether to give the title compound in a yield of 5.4 g (66.2%), mp: 133-135 ° C.

The compounds listed in Table I are prepared in a manner similar to that described for the preceding examples.

Table I

Compounds of the general formula (X) in which X =

oxygen

Connection Ri R2 R3 R4 R5 E mp.

No. ° C

1 CI H CH3 CH 3 CH3 CH 126-8 2 Η H C2H5 CH3 CH3 CH 118-9 3 CI H CH3 CH3 CH30 N 130-5 4 CI H C2H5 CH3 CH30 N 123-4 5 C00CH3 H CH3 CH3 CH3 CH. 133-5 6 COOCH3 H C2H5 CH3 CH3 N 124-6 7 C00CH3 H CH3 CH3 CH30 N 112-5 8 C00CH3 H C2H5 CH3 CH30 N 105-6 9 C00CH3 H C4H9 CH3 CH30 N 100-2 10 C00CH3 H C4H9 CH3 CH30 N 103-4 11 Η H CH3 CH3 CH30 N 125-7

Example 6

Production of a wettable powder (10 WP)

Weighed-in components: he - - active ingredient produced according to Example 2 20 silicate carrier (Zeolexr 444) - * -80,

Silica (diatomaceous earth) 80

Sodium aliphatic sulfonate dampening agent (Netzer IS) 4 Cresol-formaldehyde sulfonate dispersant (dispersant 1494) 6

Sulphite lye powder (Borresperse NA) 10

The powder mixture is comminuted in a laboratory ball mill for 30 minutes, after which it is comminuted to fine particles in an Alpine 63 C laboratory contraplex mill at speed level 70. The wettable powder composition obtained in this way contains the compound No. 4 from Table I as an active ingredient in an amount of 10% by weight.

Floatability (in 1% concentration): 86.5%.

Wet sieve residue (on a DIN 10 sieve): 0.27%.

Example 7

Production of a wettable powder (50 WP)

Weighed components: a ..

Active ingredient 150 prepared according to Example 3

Synthetic silicate carrier (Zeolex. 444) 30

Silica 50

Sodium aliphatic sulfonate (Netzer IS) 4

Cresol formaldehyde sulfonate 6

Sulphite lye powder 10

The example described in Example 6 is followed.

The wettable powder composition thus obtained contains the compound No. 2 from Table I as an active ingredient in an amount of 50% by weight.

Floatability, (in 1% concentration): 82.9%. . -. - -

Wet sieve residue (on a DIN 100 sieve): 0.43%.

Example 8

Production of a wettable powder (85 NP)

Weighed-in components: ': active ingredient prepared according to Example 4 170 synthetic silicate carrier (Sipemat 50 S) 20

Sodium oleyl methyl laurate (Arkopon T plv.) 4

Cresol formaldehyde sulfonate 6

The example described in Example 6 is followed.

The wettable powder composition thus obtained contains the compound No. 6 from Table I as an active ingredient in an amount of 85% by weight.

Floatability (in 1% concentration): 82.9%.

Wet sieve residue (on a DIN 100 sieve): 0.43%.

Example 9

Preparation of an emulsifiable concentrate (5 EC)

Weighed components: σ active ingredient 5 produced according to Example 1

Xylene. 70

Cyclohexanone 15

Calcium dodecylbenzenesulfonate (Emuisogen IP 400) 8

Fatty acid polyglycol ester (Emuisogen EL 400) 2

The active ingredient is dissolved in a mixture of xylene and cyclohexanone with stirring, and both 8 g Emuisogen IP 400 and 2 g Emuisogen EL 400 are added

Emulsifier added. After homogenization, the mixture is filtered.

The emulsifiable concentrate thus obtained contains the compound No. 8 from Table X as an active ingredient in an amount of 5% by weight.

Stability of the emulsion (1% concentrate in CIPAC A and. CIPAC. D water): stable after 2 hours.

Reversible cream formation is observed after 24 hours. Example 10

Production of an atomizable powder (5 D)

Weighed components: he

Talk 20

Silicate (Sipemat 50 S) 30 active ingredient 50 produced according to Example 5 limestone ground (M 10) 900

The mixture of active ingredient prepared according to Example 5, the carrier made of synthetic silicate and the talc are comminuted in a laboratory ball mill for 30 minutes, then comminuted in a laboratory contraplex mill of the Alpine 63 C type to fine particles. The ground material is homogenized with the limestone ground material in a laboratory powder mixer.

The atomizable powder thus obtained contains the compound No. 5 from Table I as an active ingredient in an amount of 5% by weight.

Screening residue (on a DIN 100 screen): 0.12%.

Example 11

Production of a suspension concentrate (5 'FW)

Weighed-in components: -q> active ingredient produced according to Example 2 10 sunflower oil 168 organophilic bentonite (Ivegel) 2 _.

Polyethylene alkyl ether, polyoxyethylene castor oil, ethoxylated fatty acids and sodium sulfosuccinate (Sorpol 3815) 20

The active ingredient, sunflower oil, organophilic bentonite (Ivegel) and Sorpol 3815 emulsifier are weighed into a laboratory ball mill. The suspension concentrate is comminuted together with 65% by volume of glass spheres with a diameter of 1.0 to 1.5 mm at 775 rpm for 30 minutes.

The suspension concentrate thus obtained contains the compound No. 4 from Table I as an active ingredient in an amount of 5% by weight.

Stability of the emulsion (1% concentrate in CIPAC A and CIPAC D water): stable after 30 minutes.

Example 12

Preparation of a suspension concentrate (40 FW)

Weighed-in components: α active ingredient produced according to Example 1 80 synthetic silicate. (Zeolex 444),. 6

Sodium αleylmethyl tauride (Arkopon T plv.) 4

Nonylphenyl polyglycol ether (Arkopal N 100) 10 2% xanthan gum (Kelzen S) solution 10

Water 80 80 g of the active ingredient prepared according to Example 1, synthetic silicate (Zeolex 444), sodium oleyl methyl tauride (Arkogon T) and nonylphenyl polyglycol ether (Arkopal N 100). Moisturizing dispersants and 80 g of water are weighed into a laboratory ball mill. After. Homogenization ..... the suspension concentrate is crushed together with 70 vol .-% of a filling of glass balls with a diameter of 1.0 to 1.5 mm for ~ 30 minutes. After grinding and separation from the filling, the mixture is homogenized with 20 g of 2% xanthan gum (Kelzen S) solution in an Ultra Turrax device with vigorous stirring.

The suspension concentrate thus obtained contains the compound No. 8 from Table I as an active ingredient in an amount of 40% by weight.

Floatability (in 1% concentration): 97.3%

Particle size (under 10): 91.6%

Example 13

Production of a water-dispersible granulate (-75 WDG) -

Weighed components: σ

Compound No. 3 from Table 1 as an active ingredient 375 synthetic silicate carrier 55

Polyvinylpyrrolidone (K 30 BASF product) 20

Alkylphenol ether phosphate (Atlox 5330 ICI product) 30

Mixture of polyalkylene glycol ether and polymethylene alkylaryl ether (Atlox 4896 ICI product) 20

Water 180 375 g of compound No. 3 from Table X as. active ingredient · are crushed (pre-ground) with 55 g synthetic silicate carrier in a laboratory ball mill, then the mixture is ground in a laboratory contraplex mill of the type Alpine 63 C at speed level 80 to fine particles. The granulation liquid is prepared by dissolving 20 g of polyvinylpyrrolidone, 30 g of alkylphenol ether phosphate and 20 g of a mixture of polyalkylene glycol ether and polymethylene alkylaryl ether in 180 ml of water. The ground powder mixture is placed in a FPG type 0.5 granulating machine with vortex atomization for batches. Operation · (periodically operated) introduced, and brought to a temperature of 60 to 65 ° C in a liquefied state by regulating the penetrating air flow. When the inlet temperature reaches • 30 ° C, the evaporation, the granulation liquid is started at a pressure of 1.5 bar and that

Air flow volume is increased depending on the particle growth. After introducing the granulating liquid, drying is continued until the outlet temperature reaches 36 to 38 ° C.

The granules thus produced contain compound No. 3 from Table I as an active ingredient in an amount of 75% by weight.

Floatability (in 1% concentration after 30 minutes): 93.7% particle size between 0.2 and 1 mm: at least 75%

Example 14

Production of a water-dispersible granulate (25 WDG)

Weighed components: y

Compound No. 7 from Table 1 as an active ingredient 125 synthetic silicate carrier 250

Maltodextrin binder 75

Lignin sulfonate (Sorpol 90 47 K Toko product) 30

Polyoxyethylene polyalkylaryl phenyl ether sulfate (Sorpol 5096 Toko product). . 20th

Compound No. 7 from Table 1 as an active ingredient, synthetic silicate carrier, maltodextrin binder as well as lignin sulfonate (Sorpol 90 47 K Toko product) and polyoxyethylene polyalkylaryl phenyl ether sulfate (Sorpol 5096 Toko product) surfactant are placed in a laboratory ball mill weighed in. After 30 minutes of grinding, the powder mixture is ground to fine particles in an Alpine 63 C laboratory contraplex mill. The regrind is placed in a .FPG pelletizing machine of type 0.5 with vortex atomization for -. - .- batch-wise operation (operated periodically) and brought into a liquefied state by regulating the air flow to a temperature of about 60 ° C.

When the outlet temperature reaches 28 to 30 ° C, the granulation is carried out by atomized water. After the desired particle size of about 0.5 mm has been reached, atomization of the water is stopped and drying is continued until the outlet temperature reaches 36 to 38 ° C.

The granules thus produced contain the compound No. 7 from Table I as an active ingredient in an amount of 25% by weight.

Floatability (in 1% concentration after 30 minutes): 91.85% particle size between 0.2 and 1.0 mm: at least 95%.

Example 15

Preparation of a suspension concentrate (14.5 FW)

Weighed components: qr

Compound No. 8 from Table 1 as active ingredient 2 DKA-24 (N-dichloroacetyl-N-allylglycine-N '-allylamide) as an antidote 12.5

Zeolex: 444 carriers 11.6.

Monoethylene glycol 15

Arkopon T fountain solution 3

Arkopol N-090 (nonylphenyl polyglycol ether)

Dispersant 6

Water 39.9 2% by weight of xanthan gum solution as a thickener 10

The suspension concentrate containing the active ingredient (compound No. 8 from Table I) and the DKA-24 antidote in a total amount of 14.5% by weight in a weight ratio of 1: 6.25 is divided as described in Example 12.

Example 16

Preparation of a suspension concentrate (27.0 FW)

Weighed components: cr

Compound No. 8 from Table 1 as active ingredient 2 R-25788 (N, N-diallyl-dichloroacetamide) as antidote 25

Zeolex 444 carrier 5

Monoethylene glycol 10

Arkopon T fountain solution 2.5

Arkopol N-090 dispersant 5.5

Water 42 2% by weight of xanthan gum solution as a thickener 8

The procedure described in Example 12 is followed to obtain a suspension concentrate containing the active ingredient (Compound No. 8 from Table I) and the R-25788 antidote in a total amount of 27% by weight in a weight ratio of 1: 12.5.

Example 17

Production of a wettable powder (20.25 WP)

Weighed components: g

Compound No. 4 from Table 1. as an active ingredient 1.5 AD-6 7 (N-dichloroacetyl-1-oxa-4-a zaspiro (4.5] decane) as an antidote 18.75

Zeolex 444 carrier 34.75

Silica (diatomaceous earth) 33.0

Netzer IS dampening solution 3

Dispersant 1494 4

Sulphite liquor powder 5

The procedure described in Example 6 is followed to obtain a moisturizer containing the active ingredient (Compound No. 4 from Table _I) and the AD-67 antidote in a total amount of 20.25% by weight in a 1: 12.5 weight ratio Powder ".

Example 18

Production of a water-dispersible granulate (13.5-WDG)

Weighed components: · σ

Compound No. 6 from Table 1 as active ingredient 1 CGA-92194 [N- (1,3-dioxolan-2-ylmethoxy) imino-benzene-acetonitrile] as antidote 12.5 synthetic silicate carrier 61.5

Maltodextrin binder 15

Lignin sulfonate (Sorpol 90 47 K) 6

Polyoxyethylene polyalkylaryl phenyl ether sulfate (Sorpol 5096) 4

The procedure described in Example 14 is followed to add the active ingredient (Compound No. 6 from Table I) and the antidote (CGA-92194) in a total amount of. 13.5 wt .-% in a weight ratio of 1: 12.5 containing water-dispersible granules.

Example 19

Production of a damp powder (51.2 WP)

Weighed components: he

Compound No. 2 from Table 1 as. active ingredient 20 DKA-24 as antidote 31.2

Zeolex 444 carrier 14-, 4th

Silica carrier 24.4

Netzer IS wetting agent 2

Cresol formaldehyde sulfonate 3

Sulphite liquor powder dispersant 5

The procedure described in Example 6 is followed to obtain the active ingredient (Compound No. 2 from Table I) and. to obtain the antidote (DKA-24) in a total amount of 51.2% by weight in a 1: 1.56 weight ratio of a moisturized powder.

Example 20 - -

Production of a damp powder (24.75 WP)

Weighed components: σ

Compound No. 2 from Table 1 as an active ingredient 6 MG-291 (2-dichloromethyl-2-methyl-1,3-dioxolane) as

Antidote 18.75

Zeolex 444 carrier 33

Silica carrier · 32.25

Netzer IS wetting agent 2

Dispersant 1494 3

Sulphite liquor powder dispersant ~ ...... - 5

The procedure described in Example 6 is followed to add the active ingredient (Compound No. 2 from Table I) and the antidote (MG-191) in a total amount of. 24.75 wt .-% in a weight ratio of 1: 3.125 containing composition of a moistible powder.

Example 21

Production of a dustable powder (5.2 D)

Weighed components: σ

Compound No. 5 from Table 1 as active ingredient 2 AD-67 as antidote 50

Talk 19

Carrier made of synthetic silicate (Sipemat 50 S) 29

Limestone grist (M 10 type) 900

The procedure described in Example 10 is followed to add the active ingredient (Compound No. 5 from Table I) and the antidote (AD-67) in a total amount of 5.2 wt%. Weight ratio 1:25 composition to obtain a dustable powder.

Example 22

Production of a moistible powder (21 WP) j

Weighed components: σ

Compound No. 6 from Table 1 as active ingredient 1 DKA-24 as antidote 20

Zeolex 444 carrier 30

Silica carrier 39.5

Dispersant 1494 3

Netzer IS dampening solution 2

Sulphite lye powder 4.5

The procedure described in Example 6 is followed to obtain a composition of a moisturized powder containing the active ingredient (Compound No. 6 from Table I) and the antidote (DKA-24) in a total amount of 21% by weight in a 1:20 weight ratio to obtain.

Example 23

Production of a dustable powder (6 D)

Weighed components: σ

Compound No. 4 from Table 1 as an active ingredient 10 DKA-24 as an antidote 50

Talk .15

Carrier made of synthetic silicate (Sipemat 50 S) 25

Limestone grist (M 10 type) 900

The procedure described in Example 10 is followed to add the active ingredient (Compound No. 4 from Table I) and the antidote (DKA-24) in a total amount of 6 wt%

Weight ratio 1ϊ5 containing composition of a dustable powder.

Example 24

Preparation of a suspension concentrate (22 FW)

Weighed components: q

Compound No. 2 from Table 1 as active ingredient 2 DKA-24 as antidote 20

Zeolex 444 carrier 6

Arkopon T fountain solution 4

Arkopol N-100 dispersant 10 2% by weight xanthan gum solution as a thickener 10

Water 48

The procedure described in Example 12 is followed to obtain a suspension concentrate containing the active ingredient (Compound No. 5 from Table I) and the antidote (DKA-24) in a total amount of 22% by weight in a 1:10 weight ratio.

Example 25

Greenhouse test of the postemergent effect (effect on developing plants)

The seeds of the test plants were sown in a mixture containing 1/3 part of sand, 1/3 part of clay and 1/3 part of Floresca Chemozem soil, in 200 ml plastic bottles with 4 holes on their underside.

After sowing, the soil and the small plants that came up with it were watered daily at a temperature of 20 to 26 ° under natural lighting with additional lighting for 4 hours. The composition 10 WP prepared from the compounds Nos. 3, 5, 6, 7 and 8, in each case from Table I in accordance with Example 6, was extracted using 1000 liters of water per hectare under a pressure of 4 bar using a

Greenhouse sprayer sprayed on 2 to 4-leaf plants.

The damage (injuries) to the test plants were determined in., The 2nd and 4th week following spraying. The damages . of the various test plants are given in percent; 0% means no damage and 100% means complete death.

The results are summarized in Table II. It can be seen that the compositions according to the invention have a good herbicidal action and an advantageous selectivity against the crop plants. Compounds Nos. 3, 7 and 8 were found to be particularly effective.

In the first column of Table II and the following tables, the Roman numeral I refers to Table I and the Arabic number refers to the compound number in Table I.

Table II

Postemercent effect

Compound No. Dose Death of test plants (%) (in Table 1) g / ha ORYS STEM ECHC GALA ΜΑΤΙ ZEAM HELA GLYM • TRIE ~ -----: - '"-----; · __; ·· 7 ......

1/3 270 30 100 80 100 100 20 100 80 0 90 0 100 60 80 100 0 100 30 0 30 0 100 0 40 90 0 40 30 0 10 0 100 0 30 30 0 0 0 0 1/5 270 100 100 100 80 100 100 100 100 100 1/6 270 90 100 100 35 70 100 100 80 100 90 80 100 100 30 50 90 100 50 90 1/7 270 10 100 100 60 100 10 100 70 0 - - 90 10 100 100 50 100 10 100 60 0 30 0 100 20 25 90 0 40 0 0 10 0 100 0 0 30 0 40 0 0 1/8 270 20 100 100 70 100 100 100 90 0 90 20 100 90 50 100 20 100 60 0 30 0 100 30 40 90 10 100 40 0 10 0 100 0 30 90 0 70 10 0

Abbreviations in Table II: ORYS Oryza. sativa STAND Stellaria media ECHC Echinocloa c.g. GALA Galium aparine ΜΑΤΙ Maricana inodor ZEAH Zea mays HELA Helianthus annuus GLYM Glycine max TRIE Triticum aesticum.

Example 26

Greenhouse test, the postemergent effect

The seeds of the test plants were sown in 3 repetitions in forest soil impermeable to the medium, which was located in a cardboard box perforated at the bottom with a height of 200 cm 2 and a height of 7 cm. The boxes of the individual treatments were placed on plastic troughs which were provided with a dampening cloth. After sowing, before developing the plants, the composition 10 WP prepared from compound No. 7 from Table I in accordance with Example 6 was applied to the soil surface in the boxes using a greenhouse microsprayer with a quantity of water corresponding to 1200 liters per hectare. The water supply was ensured by keeping the dampening cloth in a moist state. The test was carried out at a temperature of 20 to 28 ° C under natural lighting with additional lighting for 4 hours. The herbicidal activity of compound 7 from Table I was shown in the '4. and 6th week after spraying. The results are summarized in Table III.

Table III Preemergent Effect

Compound No. Dose death of test plants (%)

(in Table 1) g / ha Solanum Digitaria ECHC STEM TRIE

migrum adans. 1/7 250 70 50 20 100 0 1000 100 60 40 100 0

Example 27

Investigation of the effect on crop plants in the plant cultivation chamber

400 g each of arable soil (with pH 6.5,

Permeability 50 and 1.4% humus content) were weighed into plastic culture bottles, each lined with PVC, of 0.8 dm2 each. 10 pi-3737 corn seeds, · 100 striped sunflower seeds "IREG", 50 SA-114 sorghum seeds and 1 g of red millet were each sown on this soil.

After covering the seeds with 100 g of soil in each case, the treatments were carried out. In the course of these treatments, in each case doses of 10, 20, 40, 80, 160 or 320 g from the compounds No. 2, 4, 5, 6 and 8, water-dispersible granules (75 WDG) prepared in accordance with Example 13, and also Ally, part , Granstar, Glean, Logran and SL-950 control compositions per hectare applied in four replicates. The treated soil surface was again covered with an additional 100 g of soil in each area.

The bottles were placed in plant breeding chambers, watered daily to their water absorption capacity and cultivated under HGMF / D 400 sunshine replacement lamps with a daily exposure time of 16 hours. The attempt was made. evaluated on the 10th day after sowing and the green weight and sprout length of maize were determined. The results obtained are summarized in Table IV with the designation "sowing I".

The seeds of maize, sunflower and millet were sown six times in the soil from the evaluated experiment.

The results of the evaluation of these latter tests are summarized in Tables V to IX with the designations "sowing II, III, IV, V, VI".

It took 76 days from sowing I to evaluating sowing VI.

Table IV

Development of the green weight of Pi-3737 maize and the sunflower "IREG" under the effect of the treatments (given as a percentage of the untreated control)

Green weight corn Green weight sunflower

Treatments Dose of active ingredient (g / ha) 10 20 40 80 160 320 10 20 40 80 160 320

Al ly 59 48 18 8 1 70 77 67 58 68 40 1/8 7 78 78 56 44 12 119 91 79 88 68 60 1/4 81 81 82 56 33 29 145 112 112 81 72 68 1/6 84 60 22 10 3 11 121 107 97 53 65 60 1/2 98 107 95 86 71 55 125 112 109 88 53 84 1/5 62 74 22 6 8 83 86 61 74 70 59

Glean 66 37 16 10 7 60 56 49 47 53 77

Part 108 107 85 82 81 70 65 67 82 63 58 51

Logran 80 81 62 40 37 41 61 67 74 70 60 56 SL-950 96 112 111 108 99 96 111 114 102 81 50 56

Granstar 84 86 100 88 57 30 119 102 107 97 98 60

Continuation of Table IV

Development of green weight of millet and sorghum on the effect of treatments (expressed as a percentage of the untreated control)

Green weight corn Green weight sunflower

Treatments dose of active ingredient / g / ha) 10 20 '40 80 160 320 10 20 40 80 160 320

Al ly 24 76 46 67 26 13 97 83 77 56 27 7 1/8 9 21 28 52 18 14 147 126 152 141 80 84 1/4 66 32 41 27 62 26 153 144 169 125 115 165 1/6 15 61 43 50 22 6 132 102 68 14 - 1/2 66 69 85 89 67 35 136 107 107 116 94 111 1/5 78 61 88 45 6 6 115 58 19 8 2

Glean 48 67 96 42 39 21 129 85 67 67 75 46

Part 66 16 51 7 45 31 80 63 16 1 SL-950 80 40 55 34 57 15 118 91 108 54 21 17

Granstar 23 77 77 69 81 64 133 103 158 139 127 91

Logran 38 19 3 50 73 45 104 97 117 113 90 80

Table V

Results of sowing II

Green weight corn Green weight sunflower

Treatments Active ingredient dose (g / ha) 10 20 40 80 160 320 10 20 40

Al ly 133 105 107 51 35 58 46 53 72 1/8 126 109 116 100 109 65 75 72 58 1/4 104 84 125 90 120 84 100 117 121 1/6 102 137 120 83 35 10 75 100 102 1/2 91 111 127 123 118 116 65 88 124 1/5 137 121 127 58 19 23 88 129 83

Glean 98 88 65 46 19 12 70 60 63

Part 127 147 130 132 118 121 56 93 81

Logran 113 114 116 120 100 47 46 56 56 SL-950 93 100 107 127 102 130 77 88 82

Granstar 107 130 137 88 116 139 61 77 112

Continuation of table V

Green weight sunflower Green weight sorghum

Treatments Active ingredient dose (g / ha) 80 160 320 10 20 40 80 160 320

Al ly 58 42 47 105 87 74 62 17 13 1/8 68 - 75 97 82 102 35 76 100 1/4 128 122 113 99 85 85 129 129 104 1/6 61 70 58 107 51 96 41 10 1/2 114 79 82 - 58 30 97 86 98 1/5 56 51 47 88 81 82 38 2 -

Glean 53 58 79 - 136 85 95 72 60

Part 77 56 68 40 96 84 64 8 -

Logran 49 74 67 - 106 91 73 65 69 SL-950 58 86 58 42 84 89 65 34 32

Granstar 95 95 95 11 87 91 99 73 129

Table VI

Results of sowing III

Green weight corn Green weight sunflower Green weight sorghum treatments Dose of the active ingredient (g / ha) 10 20 40 80 160 320 10 20 40 80 160 320 10 20 40 80 160 320

Al ly 90 92 68 73 17 22 49 46 48 43 40 61 99 85 78 65 25 36 1/8 85 107 88 89 66 93 81 77 73 56 51 69 90 85 89 76 93 74 1/4 107 93 108 97 81 81 106 114 107 67 63 76 92 105 64. 67 66 121 1/6 113 103 68 79 75 1 93 76 70 80 51 48 90 77 25 16 11 - 1/2 93 92 86 86 78 105 107 127 96 107 100 84 83 61 60 80 97 107 1/5 97 100 83 53 32 24 102 71 81 53 54 32 89 86 85 71 10 4

Glean 75 79 76 54 34 32 54 39 67 49 54 47 108 113 113 67 67 53

Part 100 95 100 125 97 93 112 96 84 70 53 51 99 80 61 36 22 4

Logran 118 117 97 90 93 88 54 74 51 67 56 43 116 126 96 101 93 74 SL-950 100 97 115 113 98 109 83 120 100 107 64 61 83 96 62 54 36 12

Granstar 81 108 92 71 76 86 57 108 88 110 97 59 104 122 98 96 77 96 i i <

Table VII

Results of sowing IV

Green weight of corn Green weight of sunflower Green weight of sorghum

Treatments Dose of active ingredient (g / ha) 10 - 20 40 80 160 320 10 20 40 80 160 320 10 20 40 80 160 320 -

Al ly 75 56 39 44 14 14 43 43 37 34 40 35 75 93 59 54 46 42 1/8 95 97 62 66 66 74 63 40 55 50 37 50 108 100 96 86 90 80 1/4 81 90 70 84 56 48 85 83 72 68 38 55 89 93 92 111 93 104 1/6 97 81 74 53 30 - 65 69 55 53 43 36 70 109 86 82 12 19 1/2 92 102 73 77 67 77 75 54 83 87 74 55 38 88 90 88 90 122 1/5 60 7? 71 37 1 - 93 63 72 71 32 32 84 94 70 44 7 2

Glean 63 84 53 - 25 21 52 56 66 36 47 40 120 81 108 61 66 64

Part 60 93 99 128 70 94 73 66 52 46 57 40 101 72 76 28 24 3

Logran 55 99 95 85 51 57 44 67 53 50 41 30 98 94 107 89 89 81 SL-950 99 92 124 95 100 111 56 97 77 61 55 58 73 74 69 60 37 29

Granstar 78 109 117 106 84 79 76 75 76 60 106 72 98 101 93 99 110 103

Table VIII

Results from sowing V

Green weight corn Green weight sunflower Green weight sorghum treatments Dose of active ingredient (g / ha) 10 20 40 80 160 320 10 20 40 80 160 320 10 20 40 80 160 320

Ally 76 87 76 71 60 31 79 71 56 69 46 63 134 137 109 84 105 52 1/8 109 93 93 97 87 86 86 89 90 100 74 73 101 124 144 106 134 138 1/4 94 107 91 96 85 85 97 131 130 114 114 71 76 96 102 124 130 118 1/6 96 108 101 91 57 44 66 91 86 89 76 61 50 80 79 80 54 22 1/2 95 86 97 83 99 94 99 104 111 115 105 81 114 123 109 121 100 108 1/5 119 95 107 92 87 41 107 108 115 83 82 57 64 109 73 83 24 4

Glean 89 83 79 57 29 24 80 98 67 51 54 51 139 59 104 144 109 93

Part 93 100 88 117 103 99 71 84 98 91 87 41 87 75 72 86 63 36

Logran 92 108 102 98 102 92 73 70 83 79 70 148 134 86 107 105 95 117 SL-950 87 95 98 106 117 93 162 94 70 128 105 71 81 79 86 86 34 33

Granstar 95 110 98 100 99 87 115 71 88 94 120 101 151 88 87 95 106 122 i

Table IX

Results of sowing VI

j <

Green weight corn Green weight sunflower Green weight sorghum

Treatments Dose of active ingredient (g / ha) 10 20 40 80 160 320. 10 20 40 80 160 320 10 20 40 | 80 160 320

Al ly 108 113 87 83 61 50 60 79 74 77 81 52 93 123 119 104 70 53 1/8 100 90 92 76 86 85 84 86 100 97 79 71 105 103 101 82 101 95 1/4 101 91 96 101 81 81 81 109 102 132 71 66 139 110 112! 90 88 86 1/6 101 102 100 97 58 93 98 135 125 109 88 79 100 106 65 89 2 54 1/2 100 103 100 89 93 85 148 88 124 96 85 90 101 127 120 115 113 89 1/5 100 113 104 91 81 29 87 82 116 140 92 69 85 112 116 87 30 7

Glean 99 100 83 96 46 29 81 90 65 72 66 82 130 129 123 96 106 102

Part 100 89 96 126 120 124 112 137 92 90 95 81 106 93 105 122 99 52

Logran 97 96 93 108 122 102 50 92 73 55 50 58 106 119 139 103 106 95 SL-950 97 105 106 98 115 109 134 95 103 98 76 94 92 104 95 71 58 24

Granstar 95 101 93 96 97 97 92 87 102 84 105 98 112 92 105 80 106 83

Example 28

Test of herbicidal activity in a test carried out in a winter wheat crop

A control experiment with post-allergenic weeds was carried out on winter wheat in parcels of 10 m2 near the river Sebes-Körös.

The test was carried out on a Wiesenton soil type containing 3.4% organic material with a pH of 6.3. Winter wheat was used as green fodder. The seeds were sown on October 24th in a well prepared, dry seed bed at a depth of 6 to 7 cm with a row spacing formed by direct sowing.

The test was carried out on April 20 post-emergent. The weed species and their stage of development at the time of treatment were: Burweed (Galiura aparine, abbreviated to GALAP) in the 4- to 6-turn stage; red nettle · (Lamium purpureum, LAMPU) in bloom; Meadow veronica (Veronica arvensis, VERAR) in bud state at the beginning of flowering; medicinal bile (Fumaria officinalis, FUMOF) in the 6-leaf stage; Stemmiere (Stellaria media) in the flower stage; Eastern delphinium (Consolida orientalis, CONOR) 10 cm high, in the stalk-forming stage; white goosefoot (Chenopodium album, CHEAL) in the 2- to 6-leaf stage; pale orchid. (Bilderdyckia convolvulus, BILCO) in the 2 to 3 leaf stage. A plot spraying machine with propane-butane gas pressure was used to carry out the experiment. Doses of 10 to 80 g per hectare of active ingredient of compounds 4, 5, 6 and 8 from Table I were used in 500 liters of spray liquid per hectare in the form of 5 FW suspension concentrates formulated according to Example 11. The same Logran 75 DF and Granstar 75 DF cans were used for comparison.

The herbicidal and phytotoxic effects of the treatments carried out within these trials were assessed

Using a mark (scale) from 0 (ineffective) to 100 (complete disappearance) determined. These investigations were carried out 4 times (on April 27, May 4, May 25 and June 18) in the vegetation period following treatment by measuring the. Number, of tips (pieces / m2), tip length (cm) and the weight of 1000 grains, (g) performed ·. The results, which is the average of 4 repetitions, are summarized in Tables X to XVI .....

Table X

Hand-dose investigative herbicidal effect phytotoxicity treatment g / ha time GALAP LAMAM LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO% 1/8 10 I. 11 0 0! 20 0 4 0 11 21 0 II.34 20 34 16 19 15 0 50 35 0 HI. 53 79 89 91 30 72 0 85 91 0 IV.46 90 94 96 20 - 0 90 0 1/8 20 I. 20 0 0 14 o 5 0 15 23 0 11 * 40 25 35 21 23 33 8 53 46 0 m * 70 85 90 91 43 93 0 99 98 0

Iv · 56 90 94 99 23 - 0 gg gg 0 1/8 40 I. 23 0 6 18 0 8 4 29 33 13 II · 48 29 39 31 5 35 0 53 56 14 HI · 78 93 92 95 57 99 4 99 gg o IV. 75 99 99 99 30 - 0 100 100 0 I / 8 80 I. 33 0 10 21 0 4 8 33 33 18 II * 58 38 43 38 30 16 18 55 60 15 III. 94 93 96 98 88 99 13 99! 99 0 IV. 96 100 100 100 66 - 15 100 100 0

Table XI

Treatment dose dose herbicidal effect phytotoxicity treatment g / ha time GALAP IAMAH LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO% I / 4 10 I · 13 0 0 13 0 4 0 15 11 0 H * 44 25 16 21 35 15 0 36 43 0 HI.72 79 86 72 58 74 0 85 92 0 iv. 66 86 92 75 40 - 0 90 90 0! / 4 20 I. 19 0 0 15 0 0 0 16 16 0 H- 48 16 33 24 34 25 0 23 29 20 HI91 88 89 87 80 94 0 89 94 0

Iv.88 92 96 90 66 - 0 96 ioo 0

1/4 40 I. 20 0 0 19 0 0 6 18 19 75 H * 55 39 30 33 34 17 10 60 63 20 HI * 92 96 95 88 81 99 0 99 99 0 IV90 100 100 94 75 - 0 100 100 0! / 4 80 I * 23 0 5 21 0 0 5 16 28 15 II * 49 23 31 16 15 25 6 44 58 30 HI97 97 98 98 84 100 18 99 99 35 IV. 100 100 100 100 75 - 15 100 100 33 t

Table XII

Hand-dose determination herbicidal effect phytotoxicity lun1 Η / ha time GALAP LAHAM LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO% 10 I. 0 0 0 0 0 0 0 15 ii lg H * 13 0 18 13 38 21 0 30 33 33 H! · 20 10 0 0 25 25 0 41 46 35 IV * 20 0 0 0 28 - 0 37 56 30 ^ / 6 20 I. 0 0 0 0 0 0 0 14 17 20 11 · 5 21 0 10 28 23 0 40 41 33 τττ24 0 0 0 25 38 0 66 68 46 IV * ^ 2 0 0 0 31 - 0 72. 80 54

1/6 40 τ '5 0 14 5 0 0 0 26 20 24 * * - - * * * 25 21 29 3 20 15 0 45 45 36 * * - · * · -? ♦ 28 18 26 9 51 48 0 76 75 70 IV. 28 10 23 0 46 - 0 80 82 86 I // ß 80 · * · 11 0 14 8 8 0 0 34 31 21 H · 32 23 9 20 14 15 0 73 53 25 III · 30 24 32 15 61 50 0 95 99 76 IV. 25 17 20 13 60 - 0 99 100 89

Table XIII

Treatment dose dose herbicidal effect phytotoxicity lun5 g / ha time GALAP LAMAM LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO% I / 5 10 I. 0 0 0 0 0 0 0 14 11 5 11 · 0 8 0 0 36 0 0 36 26 40 111 · '19 0 0 0 34 0 0 59 54 46 IV · 20 0 0 0 34 - 0 64 66 54 1/5 20 I * 5 0 0 0 0 0 0 14 16 5 II · 8 5 0 5 40 0 0 13 23 33 III20 0 0 0 34 0 0 60 69 59

Ιν · 33 0 0 0 40 - 0 72 80 66 1/5 40 I. 10 0 10 0 0 0 0 20 14 14 H · 9 5 15 15 31 20 0 35 30 21 HI * 24 18 29 18 45 29 0 89 94 64 IV. 30 10 21 19 39 - 0 96 100 70 1/5 80 I. 14 0 11 11 9 ο 0 21 19 19 H. 23 15 25 20 34 15 0 23 33 34 HI.23 21 33 25 48 29 0 99 99 70 IV * 37 19 30 20 46 - 0 1Q0 100 86

Table XIV

Hand-dose epidemic herbicidal effect phytotoxicity lung g /} ia time GAIAP LAMAM LAMPU VERAR FUMOF STEME CONOR CHEAL BILCO%

Logran 10 I. 18 0 0 3 0 0 0 .11 14 0 75 DF II. 38 23 40 31 0 26 0 0 33 0 III. 82 78 84: 75 0 66 0 0 86 0 IV. 90 90 96! 72 0 - 0 0 82 0

Logran 20 I. 19 0 3 15 0 0 0 23 18 0 75 DF II. 40 24 41 36 15 28 0 6 43 0 III. 94 90 95 89 41 83 0 0 96 0 IV. 96 96 99 90 36 - 0 0 99 0

Logran 40 I. 21 0 15 16 13 5 0 19 19 0 75 DF II. 48 29 40 36 13 25 0 21 48 0 III. 99 98 99 97 68 98 0 0 99 0 IV. 100 100 100 100 50 - 0 0 100 0

Logran 80 I. 30 5 15 21 15 11 0 21 21 0 75 DF II. 43 35 34 33 25 28 5 10 43 0 III. 99 99 99 99 79 99 0 0 99 0.

IV. 100 100 100 100 81 - 0 100 100 0

Table XV

Treatment dose Irrigation herbicidal effect Phytotoxicity treatment g / ha Time GALAP LAMAM LAMPU VERAR FUMOF STEME CONOR CfiEAL BILCO%

Granstar 10 I. 15 0 0 0 0 0 0 6 11 0 75 DF II.18 28 38 5 15 28 0 10 15. 0 III * 84 68 68 30 36 75 0 49 72 0 IV. 91 79 83 21 34 - 0 57 89 0

Granstar 20 I. 16 0 11 6 0 6 0 14 11 o 75 DF II.38 29 39 20 15 43 0 41 48 0 HI.82 59 68 36 58 84 0 70 83 0

IV. 90 76 86 29 46 - 0 70 94 0

Granstar 40 I. 19 8 20 10 0 0 0 20 23 10 75 DF II '38 34 35 34 21 31 15 53 53 15 III 94 76 83 49 68 89 9 97 95 0 IV. 98 96 96 40 50 - 0 94 95 o

Granstar 80 I. 25 15 19 21 0 6 0 23 19 14 75 DF II.43 44 30 25 28 51 6 48 65 15 HI.97 84 91 48 79 97 19 96 98 0 IV. 98 96 96 50 70 - 10 100 100 0

Table XVI

Results of the examinations of the tips

Treatment dose number of peak number. Weight, from g / ha tips length grains 1000.

per m2 in cm per point of grains (g)

Untreated - 589 7.8 19.4 39.4 - 1/8 10 607 7.7 21.3 40.3 20 590 7.9 19.0 41.4 40 620 8.2 22.0 40.9 80 604 7.8 20.9 40.0 1/4 10 620 7.8 21.6 40.0 20 609 7.9 20.6 41.2 40 619 7.8 21.4 42.0 80 630 7, 8 22.0 40.6 1/6 10 424 7.5 14.0 42.1 20 432 3.8 13.4 42.8 40 301 3.4 7.2 44.1 80 266 3.4 6. 0 44.2 1/5 10 399 5.9 15.4 43.7 20 250 3.2 10.8 44.4 40 248 2.8 7.0 43.9 80 261 3.4 6.1 44. 8th

Logran 75WG 10 614 7.8 20.6 42.3

Logran 75WG 20 645 7.9 21.4 40.8

Logran 75WG 40 638 8.3 21.4 42.4

Logran 75WG 80 641 7.9 22.0 41.3

Granstar 75 DF 10 600 7.8 20.8 40.0

Granstar 75 DF 20 598 8.4 20.4 40.4

Granstar 75 DF 40 639 8.0 21.1 39.8

Granstar 75 DF 80 629 7.8 21.0 41.3

From the results illustrated in Tables X to XVI it can clearly be seen that between the effectiveness of the compositions according to the invention and that of the commercially available compositions used for comparison. Compositions a difference occurred. The compositions containing the compounds Nos. 4 and 8 from Table I were found to be extremely effective in late postemergent treatments on developed weeds with very strong infection. The selectivity of both compounds against crop plants is also advantageous. Because of their high phytotoxicity and their weak, possibly not useful weed control activity, the herbicidal compositions containing the compounds 5 and 6 from Table I are not suitable for weed control in a winter wheat crop.

Example 29

Examination of the effect of antidote compositions on crop plants in a plant cultivation chamber

In each case 40 g of arable soil (with a pH of 6.5, permeability of 50 and humus content of 1.4%) were put into plastic culture bottles lined with PVC film. Weighed in 0.8 dm2 surface. 10 Pi-3737 shark seeds and 10 striped sunflower seeds "IREG" were sown on this soil. The seeds were covered by 1.00 g soil and the treatments were then carried out in 4 replicates. In the course of these treatments, doses of 20 to 160 g per hectare of the active ingredients Nos. 2, 4, 5, 6- or 8 from Table I together with 250 to 500 g per hectare of the antidotes DKA-24, AD-67, R-25788, MG-191 or-CGA- 92194 in the form of. compositions formulated according to Examples 15 to 21. The treated soil surface was covered with an additional 100 g soil in each bottle.

The bottles were placed in a plant cultivation chamber and cultivated with a daily exposure time of 16 hours. The plants were grown up to their daily

Water absorption capacity sprinkled.

The experiment was carried out by determining (measuring) the rung length and the green weight on the 13th day. after treatment, evaluated. The results are summarized in Tables XVII to χτχ.

Table XVII

Development of the green weight of Pi-3737 maize under the influence of 4 treatments

'* I

Green weight of corn as a percentage of the untreated control! Dose of the active DKA-24 AD-67 R-25788 MG-191 CGA-92194 lung samei} ingredient g / ha 250 500 250 500 250 500 250 500 250 500 1/8 40 80 91 105 97 96 100 125 82 83 76 75 1/4 40 59 83 92 91 96 96 94 73 80 87 78 1/6 20 27 50 41 33 50 37 46 32 75 71 67 1/2 160 112 113 104 87 104 96 100 79 102 99 94 1 / 5 20 62 61 73 65 78 72 70 65 55 64 71

Logran 40 56 91 80 89 82 81 80 78 77 '77 65

Table XVIII

Development of the sprout length of Pi-3737 maize under the influence of the treatments

Sprout length of maize as a percentage of the untreated control treatments Dose of the active ingredient DKA-24 AD-67 R-25788 MG-191 CGA-92194 g / ha 250g 500g 250g 500g 250g 500g 250g 500g 250g 500g 1/8 40 68 84 88 91 92 88 97 78 78 71 74 1/4 40 62 77. 83 83 88 88 90 69 76 81 79 1/6 20 19 41 31 29 41x 29 37 25 35 67 66 1/2 160 91 96 92 83 97 92 95 68 89 84 86 1/5 20 48 47 53 53 62 69 60 53 45 53 57

Logran 40 40 71 74 76 80 81 87 75 74 77 68

Table XIX

“--- ---- j

Development of the green weight of striped sunflower "IREG" under the influence of the treatments

Green weight of the sunflower as a percentage of the untreated control treatments dose of the effective DKA-24 AD-67 R-25788 MG-191 CGA-92194

Seed ingredient g / ha 250 500 250 500 250 500 250 500 250 500 1/8 40 68 81 81 71 72 73 69 65. 74 51 58 1/4 40 119 79 100 84 88 88 83 106 102 93 77 1/6 20 68 48 51 60 67 55 87 61 55 61 73 1/2 160 82 75 89 100 89 85 97 106 95 84 83 1 / 5 20 78 59 69 67 70 78 70 69 89 61 64

Logran 40 71 61 52 57 54 61 59 55 50 40 42

Example 30

Test for the Effect of Antidote Compositions on Crop Plants in a Plant Cultivation Chamber.

In each case 400 g of arable soil (with a pH of 6.5, permeability of 50 and humus content of 1.4%) were weighed into culture bottles made of plastic with a surface of 0.8 dm2, each lined with PVC film. 10 Pi-3737 maize seeds and 50 SA-114 sorghum seeds were sown on this soil. The seeds were covered by 100 g soil and the treatments were then repeated in 4 replicates. In the course of these treatments, doses of 20, 40 and 80 g per hectare of the compounds No. 2, 4, 5, 6 or 8 from Table I together with 400 g per hectare of the antidote DKA-24 in the form of according to Examples 22 up to 24 formulated compositions applied. The same doses of Glean, Granstar, Ally or Teil were used together with DKA-24 Antidot for comparison. The sprayed soil surface was covered with an additional 100 g of soil in each bottle.

The bottles were placed in a plant cultivation chamber and cultivated with a daily exposure time of 16 hours. The plants were watered daily to their water absorption capacity.

The experiment was evaluated by determining (measuring) the rung length and the green weight on the 12th day after the treatment. The results are summarized in Table XX.

»

Table XX

Rung length of corn (cm) green weight of corn (g) green weight of sorghum (g) treatments dose of active ingredient g / ha + DKA-24 + DKA-24 + DKA-24 400 g / ha 400 g / ha 400 g / ha 1/8 20 70 86 71 74 125 128 40 54 82 59 76 86 90 80 39 67 43 65 68 129 1/4 20 61 90 66 87 129 127 40 47 81 59 87 103 114 80 29 65 40 72 109 .119 1 / 6 20 41 56 49 67 50 33

40 18 25 23 30 20 10 80 10 8 30 9 7 η 1/2 20 98 95 97 92 118 114 40 105 105 119 109 114 104 80 103 98 114 106 81 94 1/5 20 68 74 77 80 57 ιοο 40 50 39 60 52 60 73 80 29 40 38 5220 24

Glean 20 11 51 16 60 24 72 4 ° 12 30 19 41 66 75 80 5 10 18 11 95 66 (

Continuation of table XX

t

Rung length of corn (cm) Green weight of corn (g) Green weight of sorghum treatments Dose of active ingredient g / ha + DKA-24 + DKA-24 + DKA-24 400 g / ha 400 g / ha 400 g / ha

Granstar 20 90 76 84 83 62 120 40 86 77 84 81 115 160 80 84 74 85 72 79 130

Al ly 20 27 49 41 63 112 58 40 16 34 24 43 106 53 80 13 24 24 33 94 46

Part 20 98 - 105 75 40 98 - 109 15 80 90 96 11

Claims (6)

1. Substituted sulfonylurea derivative · general

Formula. (Γ) - where Ri.. represents hydrogen, halogen, Cx_4-alkoxy, halo-C ^ -alkoxy, Cx_3-alkylsulfonyl or a group of the formula CORe; Rz represents hydrogen, Cx_3-alkyl or phenyl; R3 Ci_6-alkyl, C3_6-alkenyl, a Cx_3-alkoxyalkyl group. represents one or more halogens substituted C2_4-alkyl or a benzyl group, R4 and R5 each independently of one another a C ^ alkyl, a C1_4 alkoxy group, halogen, Cx_3 alkylamino or di (C ^ alkyl) amino or Is Cx.3-alkylthio; R $ represents a Cx.4-alkoxy, C3.6-alkenyloxy, C3_6-alkoxyalkyl, Cx_3-alkylamino, di (Cx.3-alkyl) amino, piperazinyl or morpholinyl group; X represents oxygen or sulfur; and E represents a methine group or nitrogen, and also its salts. (Priority: 01/31/1990) 2. Herbicidal composition containing a substituted sulfonylurea derivative, which as an active ingredient. substituted sulfonylurea derivative of the general formula (I) in which Rx represents hydrogen, halogen, Cx ^ alkoxy, halo-Cx_4-alkoxy, Cx_3-alkylsulfonyl or a group of the formula CORe; R2 represents hydrogen, Cx_3-alkyl or phenyl; R3 is Cx.o-alkyl, C3_6-alkenyl, a Ci_3-alkoxyalkyl group, C2_4-alkyl or a benzyl group substituted by one or more halogens, R4 and Rs each independently of one another are a Ci_4-alkyl · - ,. a .. C ^ alkoxy group, halogen, Ci.3-Alkyla11u.no or di (Ci.3-alkyl) amino or Ci_3-alkylthio mean; R6 represents a C 1-4 alkoxy, C3.6-alkenyloxy, C3_a-alkoxyalkyl, ... Ci.3-alkylamino, di (Ci_3-alkyl) amino, piperazinyl or morpholinyl group; and E represents a methine group or nitrogen, or a salt thereof. (Priority: 31.01.1990) 3. Composition as claimed in claim 2 in the form of a wettable powder. (Priority: 01/31/1990) 4. Composition as claimed in claim 2 in the form of granules. (Priority: 01/31/1990) 5. Antidote-containing herbicide composition, comprising a substituted sulfonylurea derivative as an active ingredient and an antidote, which comprises a substituted sulfonylurea derivative of the general formula · (I), wherein R1 # R2, R3, R4, R5, X and E are as defined in claim 1, or its salt as an active ingredient and an antidote, preferably DKA-24 (chemically N-dichloroacetyl-N-allylglycine-N'-allylamide), AD-67 (chemically N-dichloroacetyl-1- oxa-4-azaspiro [4.5] decane), R-25788 (chemical N, N-diallyl dichloroacetamide), MG-191 (chemical 2-Οΐσ1ι1ο: πηβ · ϋιγ1-2-πΐ0ί1 ^ 1-1,3-dioxolane) , CGA-92194 (chemically N- (1,3-dioxolan-2-ylmethoxy) imino-benzeneacetonitrile), or TI-35, in a total amount of 0.01 to 95 wt .-%, preferably 2. to 80 wt. -% in a weight ratio of 1: 1 to 1:50 (of the active ingredient to the antidote). (Priority: December 19, 1990.) 6. A process for the preparation of a substituted sulfonylurea derivative of the general formula (I) wherein

'. Rj represents hydrogen, halogen, C 1-4 alkoxy, halo-C1_4-alkoxy, C 1-4 alkylsulfonyl or a group of the formula COR6; r2 represents hydrogen, C1_3-alkyl or phenyl; R3 represents Cx.e-alkyl, C3_6-alkenyl, a Ci_3-alkoxyalkyl group, C2_4-alkyl or a benzyl group substituted by one or more halogens, R4 and R5 each independently represent a Ci_4-alkyl, a Cj._4 -Alkoxy ~ group, halogen, Ci_3-alkylamino or di (Ci_3-alkyl) amino or C1_3-alkylthi0; R6 represents a C ^ alkoxy, C3.6 alkenyloxy, C3_6 alkoxyalkyl, C ^ alkylamino, di (C ^ alkyl) amino, piperazinyl or morpholinyl group; and E represents a methine group or nitrogen, and also its salts, which a) reacting an isocyanate or isothiocyante of the general formula (IV),

(IV) wherein R3 is as defined above with an aminopyrimidine or aminotriazine derivative of the general formula (III)

(III) - wherein the substituents are as defined above, at a temperature of 0 to 50 ° C, preferably 20 to 30 ^ G, or b). the reaction of a sulfonyl carbamate of the general formula (V) ^ - ''

(V) wherein Rx is as defined above and R represents a phenyl group, with an aminopyrimidine or aminotriazine derivative of the general formula (III) at a temperature of 25 to 120 °, preferably at 60 to 90 ° C, or

c) reacting a carbamoyl chloride of the general formula (VI) (VI) in which the substituents are as defined above, with an alkali metal salt of a sulfonamide derivative of the general formula. (II)

(II) wherein the substituents are as defined above, at a temperature between -10 ° C and 50 ° C, preferably at 0 to 25 ° C, or d) reacting an N-pyrimidinyl or N-triazinyl carbamate of the general formula ( VII)

(VII) wherein the substituents are as defined above, with a sulfonamide derivative of the general formula (II), wherein the substituents are as defined above, at a temperature between 20 and 80 ° C, preferably at 20 to 40 ° C, or e) reacting a sulfonyl chloride of the general formula (VIII)

(VIII) · - in which the substituents are as defined above, with an aminopyrimidine or aminotriazine derivative of the general formula (III) in which the substituents are as defined above, at a temperature of 20 to 120 ° C., preferably at 60 to 90 ° C in an inert organic solvent or in a mixture of inert organic solvents, then optionally converting the compound thus obtained 'of the general. Formula (I) with an alkali metal or alkaline earth metal hydroxide, an amine or quaternary ammonium halide in its salt, separating the obtained compound of general formula (I) or its salt by evaporating off the solvent (s) and, if necessary , their recrystallization by a method known per se. (Priority: 01/31/1990)